Provided herein is a cyclic imide slurry composition and processes for forming and/or using such a composition. The slurry composition comprises solid cyclic imide and organic liquid, such as liquid alkylbenzene, liquid cyclohexane, and/or liquid organic alcohol (such as cyclohexanol). The slurry composition may find particular use in processes in which the cyclic imide serves as an oxidation catalyst (e.g., as a radical initiator). For instance, the slurry composition may be useful in the oxidation of a liquid alkylbenzene such as cyclohexylbenzene to corresponding 1-cyclohexyl-1-phenyl hydroperoxide. Such an oxidation reaction may further be part of an integrated process for the production of phenol and/or cyclohexanone from benzene via hydroalkylation to form cyclohexylbenzene.

Provided herein is a cyclic imide slurry composition and processes for forming and/or using such a composition. The slurry composition comprises solid cyclic imide and organic liquid, such as liquid alkylbenzene, liquid cyclohexane, and/or liquid organic alcohol (such as cyclohexanol). The slurry composition may find particular use in processes in which the cyclic imide serves as an oxidation catalyst (e.g., as a radical initiator). For instance, the slurry composition may be useful in the oxidation of a liquid alkylbenzene such as cyclohexylbenzene to corresponding 1-cyclohexyl-1-phenyl hydroperoxide. Such an oxidation reaction may further be part of an integrated process for the production of phenol and/or cyclohexanone from benzene via hydroalkylation to form cyclohexylbenzene.

Disclosed is (i) a process of making phenol and/or cyclohexanone from cyclohexylbenzene including a step of removing methylcyclopentylbenzene from (a) the cyclohexylbenzene feed supplied to the oxidation step and/or (b) the crude phenol product (ii) a phenol composition and (iii) a cyclohexylbenzene composition that can be made using the process.

Disclosed is (i) a process of making phenol and/or cyclohexanone from cyclohexylbenzene including a step of removing methylcyclopentylbenzene from (a) the cyclohexylbenzene feed supplied to the oxidation step and/or (b) the crude phenol product (ii) a phenol composition and (iii) a cyclohexylbenzene composition that can be made using the process.

Disclosed are processes and systems for oxidizing cycloalkylbenzene such as cyclohexylbenzene to make an oxygenate such as a hydroperoxide thereof. A liquid distributor having multiple liquid ingress ports is used for supplying a cycloalkylbenzene-containing liquid into an oxidation reactor in the form of liquid streams forming part of the reaction medium. A gas distributor distributing an O.sub.2-containing gas into the reaction medium in the form of gas streams is preferably located below the liquid distributor. Preferably the gas bubbles upwards in the reaction medium. The agitation and mixing provided by the liquid streams, gas streams/bubbles result in sufficient homogeneity of cycloalkylbenzene concentration, cycloalkylbenzene hydroperoxide concentration, dissolved oxygen concentration, and temperature in the liquid phase.

Disclosed are processes and systems for oxidizing cycloalkylbenzene such as cyclohexylbenzene to make an oxygenate such as a hydroperoxide thereof. A liquid distributor having multiple liquid ingress ports is used for supplying a cycloalkylbenzene-containing liquid into an oxidation reactor in the form of liquid streams forming part of the reaction medium. A gas distributor distributing an O.sub.2-containing gas into the reaction medium in the form of gas streams is preferably located below the liquid distributor. Preferably the gas bubbles upwards in the reaction medium. The agitation and mixing provided by the liquid streams, gas streams/bubbles result in sufficient homogeneity of cycloalkylbenzene concentration, cycloalkylbenzene hydroperoxide concentration, dissolved oxygen concentration, and temperature in the liquid phase.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.

Aromatic compositions useful in various applications, such as aromatic fluid solvents and high temperature heat transfer fluids, are provided herein. Also provided are advantageous methods for obtaining the aromatic compositions, utilizing hydroalkylation of precursor aromatic hydrocarbons such as benzene, toluene, xylene, and the like. Particularly preferred aromatic compositions include one or more of cycloalkylaromatic, dicycloalkylaromatic, biphenyl, terphenyl, and diphenyl oxide compounds. The aromatic compositions may be blended with an aromatic solvent or other aromatic fluid comprising one or more of alkylnaphthalenes, alkylbenzenes, and naphthalene, e.g., to form a useful aromatic fluid solvent, or the aromatic compositions may be utilized as high temperature heat transfer fluids (with or without additional blend components).